Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives
Zhang, Chao-Bo1; Liu, Yang1; Liu, Zheng-Fen1; Duan, Sheng-Zu1; Li, Min-Yan3; Chen, Wen1; Li, Yan2; Zhang, Hong-Bin1; Yang, Xiao-Dong1
2017-04-15
Source PublicationBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume27Issue:8Pages:1808-1814
AbstractThe synthesis of a series of novel 4-substituted 2,3,6,7-tetrahydrobenzo [1,2-b;4,5-b']difuran-1H-imidazolium salts is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. Results suggest that the 5,6-dimethyl-benzimidazole or 2-methyl-benzimidazole ring, and substitution of the imidazolyl-3-position with a 2-naphthylmethyl substituent or 2-naphthylacyl substituent, were important to the cytotoxic activity. Notably, 3-(2-Naphthylmethyl)-1-(2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-y1)methyl)-1H-5,6-dimethyl-benzimidazol-3-ium bromide (42) was found to be the most potent derivative against five human tumor cell lines with 1050 values of 1.06-4.34 mu M and more selective towards SMMC-7721, A549 and SW480 cell lines. 3-(2Naphthylacy1)-1-(2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-yl)methyl)-1H-2-methyl-benzimidazol- 3-ium bromide (37) showed higher selectivity to SMMC-7721 and MCF-7 cell lines with IC50 values 2.7-fold and 8.4-fold lower than DDP. Study regarding to the antitumor mechanism of action showed that compound 37 could induce cell cycle G1 phase arrest and apoptosis in SMMC-7721 cells. (C) 2017 Elsevier Ltd. All rights reserved.
KeywordTetrahydrobenzodifurans Imidazolium Salts Cytotoxic Activity Cell Cycle Apoptosis
DOI10.1016/j.bmc1.2017.02.053
Indexed BySCI
Language英语
WOS IDWOS:000399262600033
Citation statistics
Cited Times:15[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/51196
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Peoples R China
3.Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
Recommended Citation
GB/T 7714
Zhang, Chao-Bo,Liu, Yang,Liu, Zheng-Fen,et al. Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2017,27(8):1808-1814.
APA Zhang, Chao-Bo.,Liu, Yang.,Liu, Zheng-Fen.,Duan, Sheng-Zu.,Li, Min-Yan.,...&Yang, Xiao-Dong.(2017).Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,27(8),1808-1814.
MLA Zhang, Chao-Bo,et al."Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 27.8(2017):1808-1814.
Files in This Item: Download All
File Name/Size DocType Version Access License
zhang2017.pdf(1192KB)期刊论文作者接受稿开放获取CC BY-NC-SAView Download
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Zhang, Chao-Bo]'s Articles
[Liu, Yang]'s Articles
[Liu, Zheng-Fen]'s Articles
Baidu academic
Similar articles in Baidu academic
[Zhang, Chao-Bo]'s Articles
[Liu, Yang]'s Articles
[Liu, Zheng-Fen]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Zhang, Chao-Bo]'s Articles
[Liu, Yang]'s Articles
[Liu, Zheng-Fen]'s Articles
Terms of Use
No data!
Social Bookmark/Share
File name: zhang2017.pdf
Format: Adobe PDF
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.